Decanal → HCID 24807657, compound

HRID 1040276Notes

Reaction equation

HRID 1040276 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].[O-]S([O-])(=O)=O.[Mg+2].[CH:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].CCN(CC)CC.[BH4-].[Na+]>CO.C1COCC1>[CH2:18]([NH:6][C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[C:4]([O:3][CH3:2])=[O:11])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 5

HCID 8175DecanalHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 2723695Leucine methyl ester hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 24807657HCID 24807657, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to the general procedure as described in Example 1a using L-leucine methyl ester hydrochloride (1 gm, 5.5 mmol), THF (20 mL), MgSO4 (1.12 gm, 9.35 mmol), decanal (2.06 mL, 11.0 mmol), Et3N (767 μL, 5.5 mmol), sodium borohydride (416 mg, 11.0 mmol), and methanol (25 mL) to give 11b (800 mg, 51%) in FIG. 2. 1H NMR (500 MHz, CDCl3): δ 0.88-0.98 (9H, m), 1.2-1.37 (15H, m), 1.42-1.54 (4H, m), 1.71 (1H, heptet), 2.42-2.5 (1H, m), 2.53-2.6 (1H, m), 3.29 (1H, t, J=7.32 Hz), 3.74 (3H, s). ESI-MS: 308.1 (M+23).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-b694a139c32e4af4b3633da0c9f1529d
Source dataset
uspto-grants-2013_10
Patent number
US08552208B2

Reaction notes

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